How to Start Difficult Conversations with Your Boss or Co-Workers

The first sixty seconds of a difficult conversation are often the hardest. What do you say? Should you dive right in? Start with some small talk? Hit them with a compliment first, then the tough issue, then another compliment? (Hint: Don’t do that!)

The good news is, Susan Scott has a fantastic framework from Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time that helps walk you through how to start a tough conversation. She calls the first part of a fierce conversation the opening statement. You can read more about it in her book. Here, I am going to give you the down and dirty version and some specific examples of what these opening statements to a confrontation conversation might sound like between a Force Multiplier and their Principal or their colleagues.

Opening Statements for Difficult Conversations at Work

Example #1: A Difficult Conversation with Your Principal

You have been working with your Executive as their Executive Business Partner for 5 months. You feel confident with the day-to-day responsibilities of the role, but are not quite clicking with your Executive. You also know that to operate at the level you are accustomed to, to grow your career, to help lead, and to provide all the value you know you bring to the role, you need to be working more closely with your Executive. One-to-one meetings are imperative to making this happen, and yet, those meetings are constantly being scheduled over (by your boss’s request even though you protest) or simply missed altogether. You have tried several tactics to change this to no avail. It is time for a fierce conversation.

There are seven components to an opening statement in a difficult conversation:

1. Name the issue. Let’s say you need to confront your boss about not having a structured calendar and, in particular, the fact that they constantly move, schedule over, or completely ignore your 1-on-1 time on the calendar. With less face time with your Executive, you are finding it difficult to build a cohesive working relationship and, beyond that, the necessary clarity you need to do your job well. With all of this to consider, the next time you meet with your Executive you might say, “Pat, I want to talk with you about the effect our canceled meetings are having on me, our partnership, and the organization.”

2. Select a specific example that illustrates the behavior or situation you want to change. Your Executive may not even realize how frequently they are canceling meetings, or the effect it is having on you. Specificity is key. You could say, “For example, over the past 10 weeks, we have only kept two of our scheduled weekly meetings on June 10 and July 5. Since the beginning of the year, our weekly one-to-one meetings have been infrequent and unpredictable.”

3. Describe your emotions about this issue. As uncomfortable as it might be, clearly stating how it makes you feel carries some weight in the conversation. But don’t get carried away—state clearly and succinctly how the issue is affecting you, “I feel dismissed, frustrated, and unsure of how to proceed.”

4. Clarify what is at stake. You must explain why the issue is important and why it needs to be solved now. This is not a time to lay blame, but rather to interrogate reality and lay the issue out on the table, “I believe that my ability to effectively support you, my career growth, as well as the reputation of the Executive Office is at stake. I deeply believe in the mission of the organization and I know that I have more to offer to you and to this position. Without regular meetings with you, I feel like my hands are often tied in taking additional projects off your plate, anticipating your needs, understanding your goals and the greater context of the business in order to proactively make decisions and support you at the high level that you deserve, and that I expect of myself. Our team members watch what we both do and role model their behaviors after what they see in the Executive Office. I think our reputation as strategic partners is at stake if we continue to demonstrate that our meeting is the least important to each other and to the company.”

5. Identify your contribution to this problem. If you truly do not think you contributed in any way to the problem, leave this step out. However, 99% of issues have your fingerprint on them too. Taking ownership of your part in the issue is what leadership is all about, “I have contributed to this problem by not letting you know months ago how frustrated I was. For that, I am sorry.”

6. Indicate your wish to resolve the issue. You likely wouldn’t be bringing the conversation to light if you didn’t want to find a mutually beneficial solution or come to some sort of understanding. Express that desire and restate the initial issue so that it doesn’t get lost in the opening statement, “I want to resolve this issue and the effects our canceled meetings are having on me, our partnership, and on the organization.”

7. Invite your partner to respond. This is where the opening statement shifts to a conversation, “I want to understand and learn from your perspective. What are you seeing and thinking from where you sit?” Ask your question and then stop talking. Let silence do the heavy lifting.

Here is the opening statement in its entirety (remember – 60 seconds or less!):

“Pat, I want to talk with you about the effect our canceled meetings are having on me, our partnership, and the organization. For example, over the past 10 weeks, we have only kept two of our scheduled weekly meetings on June 10 and July 5. Since the beginning of the year, our weekly one-to-one meetings have been infrequent and unpredictable. I feel dismissed, frustrated, and unsure of how to proceed. I believe that my ability to effectively support you, my career growth, as well as the reputation of the Executive Office is at stake. I deeply believe in the mission of the organization and I know that I have more to offer to you and to this position. Without regular meetings with you, I feel like my hands are often tied in taking additional projects off your plate, anticipating your needs, understanding your goals and the greater context of the business in order to proactively make decisions and support you at the high level that you deserve, and that I expect of myself. Our team members watch what we both do and role model their behaviors after what they see in the Executive Office. I think our reputation as strategic partners is at stake if we continue to demonstrate that our meeting is the least important to each other and to the company. I have contributed to this problem by not letting you know months ago how frustrated I was. For that, I am sorry. I want to resolve this issue and the effects our canceled meetings are having on me, our partnership, and on the organization. I want to understand and learn from your perspective. What are you seeing and thinking from where you sit?

Here’s an example of what a fierce conversation might look like with a colleague:

Example #2: A Difficult Conversation with a Colleague

You have just been promoted to Chief of Staff at your company and have a new Executive Assistant reporting directly to you. While the Executive Assistant is new to your company, they are not new to the EA role. In the first 30 days, you clearly (or so you thought) outlined your expectations around how to best communicate with internal and external stakeholders, and how you and your Executive expected the company to be represented. You have had a few feedback conversations, but the issue persists. You are now nearing month four and need to move on from a feedback conversation to a confrontation conversation.

Opening statement for example #2:

“Sam, I want to talk with you about the effect your communication style has on me, Jennifer [CEO], and the reputation of our company. For example, on January 10 you told our Director of Operations that Jennifer didn’t have time to meet with them. Later that week, on two separate occasions, I heard you answer the phone in an abrupt and dismissive manner to the stakeholder on the other end. I am concerned that you have not taken my previous feedback seriously and I am worried about the potential consequences if this persists. There is a great deal at stake here. You are the first impression people get of our organization, as well as an important representative of the Executive Office. Our reputation, internal relationships, and future partnerships are at stake. I recognize that my contribution to this issue is that I didn’t make it clear that this was the expectation, not a suggestion, for your role. I also did not provide scripts or the opportunity to role-play handling various situations. For that, I apologize. I want to resolve this issue and the effect your communication style has on me, Jennifer, and our company. I want to understand what is happening from your perspective. Please talk to me about what you are seeing and thinking.

You can see that the cadence of these two opening statements is the same. They frame the issue, give specific examples, explain how you’re feeling, identify what is at stake, take ownership over your contribution to the problem, share your desire to resolve the issue, and ask the other party to respond.

That is where the conversation really begins, and together you can respectfully and effectively come to an understanding of the issue and a resolution on how to move forward.

The next time you need to have a tough conversation, pull out this framework and map out the conversation. Write it down and practice it out loud. You may even want to bring the script with you to the meeting. If anyone has a problem with it just say something simple like, “This conversation is very important to me. I may reference my notes so that I don’t miss anything.” Who’s going to argue with that?

Remember, the conversation is the relationship. If you want to continue to strengthen and deepen your relationships and grow in your leadership, you will need to be engaging in fierce conversations regularly. The opening statement is a great place to start. To go deeper, check out this post about how to have fierce conversations at work.

Original post shared on July 15, 2021.

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